CAS 86867-01-8|SAM chloride dihydrochloride|Active methionine|[(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium chloride|AdoMe...

General Information

Structure

Molecular Formula

C₁₅H₂₃ClN₆O₅S

Molecular Mass

434.89832

Exact Mass

434.11391655

Charge

InChI

InChI=1S/C15H22N6O5S.ClH/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21;/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25);1H/t7-,8+,10+,11+,14+,27?;/m0./s1

InChIKey

DYFPQIYEZQULMZ-XKGORWRGSA-N

Canonic Smiles

C[S+](C[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N)CC[C@@H](C(=O)O)N.[Cl-]

Isomeric Smiles

C[S+](CC[C@@H](C(=O)O)N)C[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)O)O.[Cl-]

Calculated Properties

JChem

Acid pKa

1.7050823

H Acceptors

H Donor

LogD (pH = 5.5)

-5.2821784

LogD (pH = 7.4)

-5.3258553

Log P

-5.3224516

Molar Refractivity

96.2349

Polarizability

38.568764

Polar Surface Area

182.63

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

Synonyms

SAM chloride dihydrochlorideActive methionineAdoMetS-(5′-Adenosyl)-L-methionine chloride dihydrochloride5'-[[(3S)-3-Amino-3-carboxypropyl]methylsulfonio]-5'-deoxyadenosine DisulfateL-S-Adenosylmethionin DisulfateS-Adenosylmethionine DisulfateAdemetionine DisulfateS-Adenosyl-L-methionine Disulfate5'-[(L-3-Amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine DisulfateS-(5'-Adenosyl)-L-methionine Disulfate Salt (Synthetic)(Mixture of Diastereomers)Active Methionine Disulfate

IUPAC name

[(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium chloride

IUPAC Traditional name

SAMe chloride

Names and Identifiers

Registration numbers

PubChem SID

CAS Number

Beilstein Number

EC Number

MDL Number

PubChem CID

Registration numbers

Properties

Physical Property

Safety Information

German water hazard class

-20°C

Download link

Hygroscopic, -20°C Freezer, Under Inert Atmosphere

Product Information

≥80%

from yeast (L-Methionine enriched)

dry ice

Download link

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Sigma Aldrich

A7007

Analysis Note
Purity based on UV and HPLC.
Caution
This material is 80-90% pure when prepared, but is very unstable. As much as 10% purity loss per day at 25 °C has been noted.
Biochem/physiol Actions
Methyl donor; cofactor for enzyme-catalyzed methylations, including catechol O-methyltransferase (COMT) and DNA methyltransferases (DNMT). Although present in all cells, it is concentrated in liver where 85% of all methylation reactions occur. It is also involved in regulating liver function, growth, and response to injury.

TRC

A291530

Methyl donor; cofactor for enzyme-catalyzed methylations, including catechol O-methyltransferase (COMT) and DNA methyltransferases (DNMT). Although present in all cells, it is concentrated in liver where 85% of all methylation reactions occur. It is also

Molecule Details

References

PubChem Literature

From Data Sources

• Friedel, H., et al.: Drugs, 38, 389 (1989)

• Lu, S., et al.: Int. J. Biochem. Cell Biol., 32, 391 (1989)

• Amin, K., et al.: Pharm. Res., 18, 914 (1989)

References

Bioactivity

PubChem BioAssay

Bioactivity